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AI Can’t Empathize: How Pro Bono Service is the Secret to Building Human Skills at Work

March 12, 2026 All

AI Can’t Empathize: How Pro Bono Service is the Secret to Building Human Skills at Work

By Elaine Mason, Taproot’s Chief Strategy Officer

AI is accelerating faster than expected, and leaders know that human skills are the differentiators that technology can’t replicate. Yet the way we attempt to build these skills still looks like it did decades ago.

I have been in leadership roles since 1996, and if there is one thing I’ve learned through the years, it’s that you cannot “teach” someone how to lead in a vacuum. Frameworks matter, but until someone is standing in a room with a passionate nonprofit founder and a limited budget trying to align a board of directors on a mission-critical strategy, they haven’t truly practiced the skill.

I learned this early in my career when I was given the opportunity to lead an advisory board for a startup nonprofit. I was young, eager, and a bit in over my head. But that pro bono experience was my crucible. The leadership challenges I faced there didn’t just test my critical thinking and problem-solving; they forged them in ways a classroom simply couldn’t provide.

Today, as gig work, hybrid teaming and AI continue to transform how work gets done, the need for those uniquely human capabilities have never been higher. Taproot’s Human Skills at Work report reveals a troubling disconnect: while 82% of professionals believe human skills are just as important as technical ones, most organizations are still trying to build those skills using outdated, traditional learning and development models.

The “Last Mile” of Learning

We are currently in a massive upskilling race. Global giants like Microsoft and Amazon are pouring billions into reskilling initiatives. But look closer at those programs, and you’ll find they are heavily weighted toward technical certifications and STEM-based learning. That is a miss. While technical literacy is a solid foundation, human skills like judgment, empathy, and adaptive collaboration represent the “last mile” between AI and actual business value. According to a recent AACSB Insights report, as AI takes over more routine tasks, our teams and leaders must become “irreplaceably human” to stay relevant.

The problem? You can’t learn judgment from a slide deck. Taproot’s study found that while traditional training is effective for technical skills like data literacy or prompt engineering, it falls short when it comes to building the relational and adaptive skills required to thrive today.

Pro Bono Service as a Human Skills Development Engine

This is where pro bono service moves from being an engagement and community focused CSR activity to a must-have talent development strategy. Taproot’s study found that experiential learning, specifically pro bono service, consistently outperforms traditional training in five critical areas:

More than 70% of professionals rated pro bono service as effective for developing 5 vital human skills Problem Solving Collaboration Adaptability Communication Relationship Building
    • Problem Solving: 73% of respondents found pro bono effective, compared to just 48% for traditional training.
    • Relationship Building: 70% effectiveness via pro bono vs. 38% in the classroom.
    • Collaboration: 73% effectiveness via pro bono vs. 48% in the classroom.
    • Adaptability: 70% effectiveness via pro bono vs. 38% in the classroom.
    • Communication: 71% effectiveness via pro bono vs. 64% in the classroom.

Why is pro bono service so much more effective? Because it simulates the human skills that have become highly critical in every workplace. It places professionals in environments defined by ambiguity, limited resources, and high-stakes purpose. It forces teams and leaders to be empathetic, to listen deeply, and to create value collaboratively.

This moment requires leaders to rethink their learning models. Traditional training still has a place. But if your organization is relying solely on courses and certifications to build future ready talent, you’re missing the effective learning modality that pro bono service provides.

The takeaway is clear: Human skills cannot be built through theory alone. They must be practiced in real world environments. – Elaine Mason

We need to stop treating social impact and learning as separate buckets. When we integrate pro bono into our core learning strategy, we don’t just help the nonprofit sector; we build more adaptable, AI-ready teams.

Why Taproot Is Leaning In

Taproot exists to design and enable pro bono service that puts professional expertise to work where it is needed. Increasingly, our role is to enable organizations to build the human capabilities that define modern leadership. This research reinforces what Taproot has observed for years: Pro bono is not just good for the community; it is a high impact, scalable engine for talent development. Pro bono isn’t simply volunteering. It’s learning infrastructure for the future of work, and Taproot is committed to building an impactful, scalable engine for talent development.

Join the Conversation

The nature of work has changed. Our talent and learning strategies must evolve with it. I invite you to:

Let’s stop talking about human skills in theory and start building them through experiences that challenge, stretch, and transform. Let’s start doing it pro bono.

 

About the author:

Elaine Mason is a strategy and HR executive focused on the intersection of workforce transformation and purpose. As Chief Strategy Officer at Taproot Foundation, she is helping shape the future of pro bono and advancing research on human skills in the AI-enabled workplace. Elaine previously held senior leadership roles at Cisco, American Express, and Paramount Global and is a frequent speaker on the future of work and people analytics.

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